Cyclohexyl methyl ketone → 1-Cyclohexyl-2-(4-cyclohexyloxy-phenyl)-ethanone

Temperature

90 °C

A stirred suspension of 1-bromo-4-cyclohexyloxy-benzene (3.92 mmol, 1.0 g), cyclohexylmethylketone (5.92 mmol, 0.83 mL), (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.88 mmol, 1.17 g), tris(dibenzylideneacetone)dipalladium(0) (0.78 mmol, 0.72 g), and potassium t-butoxide (7.84 mmol, 0.88 g) were heated to 90° C. for 12 h in a sealed vial. The reaction was cooled and partitioned in water (50 mL) and diethyl ether (50 mL). The mixture was filtered through fluted filter paper and the layers were separated. The aqueous layer was washed with diethyl ether (3×20 mL). The combined organic layers were washed with brine (10 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified on a 24 g SiO2 cartridge using an ethyl acetate/hexanes gradient to give 1-cyclohexyl-2-(4-cyclohexyloxy-phenyl)-ethanone (0.35 g).

1. temperatureThe reaction was cooled
2. custompartitioned in water (50 mL)
3. filtrationThe mixture was filtered
4. filtrationthrough fluted filter paper
5. customthe layers were separated
6. washThe aqueous layer was washed with diethyl ether (3×20 mL)
7. washThe combined organic layers were washed with brine (10 mL)
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customThe crude product was purified on a 24 g SiO2 cartridge

ORD record

ord-e638a892f4e34f2da1e1ed20d512a3bc

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09045461B2